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5 Sherwood Road, 
Windham, NH 03087

$1,599,000


4

Beds


4

Baths


5,112

Sq Ft


Single Family

Active

Listed by

Shannon Dipietro

Dipietro Group Real Estate

603-216-5086

Last updated:

July 28, 2026, 10:56 AM

MLS#

5099575

Source:

PrimeMLS

About This Home

5 Sherwood Road

Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering four spacious bedrooms and a beautifully designed walk-out lower-level in-law suite, this remarkable home delivers the perfect blend of sophistication, comfort, and versatility. From the moment you enter the grand two-story foyer, you'll appreciate the impeccable craftsmanship, classic architecture, and custom millwork found throughout. The thoughtfully designed floor plan features a private home office, an elegant formal dining room ideal for entertaining, and a warm, inviting family room centered around a stunning fireplace. At the heart of the home, the expansive kitchen opens seamlessly to the living spaces, creating the perfect gathering place for family and friends. Just beyond, a breathtaking sunroom overlooks the private backyard, filling the home with natural light and providing direct access to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room is an entertainer's dream, showcasing custom millwork, a beautifully crafted built-in bar, and the perfect setting for movie nights, game days, or hosting guests. The luxurious primary suite serves as a true retreat with a spa-inspired bath, while the additional bedrooms are all exceptionally spacious. The walk-out lower level offers a complete in-law suite with its own living space, providing exceptional flexibility for multigenerational living, extended family, guests, or an au pair. Step outside to your own private resort where the expansive composite deck overlooks a spectacular gunite inground pool, all surrounded by professionally designed landscaping that creates an unmatched sense of privacy across 3.5 acres. A classic farmer's porch welcomes you home, completing this extraordinary property where timeless architecture, luxurious finishes, and seamless indoor-outdoor living come together.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1999

Price Summary

1,599,000

$312 per Sq. Ft.

MLS #:

5099575

Last Updated:

July 28, 2026, 10:56 AM

Added:

15 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

2

Interior

Living Area:

5,112 Sq. Ft.


Structure

Structure

Building Area:

6,154 Sq. Ft.

Year Built:

1999


Lot

Lot Size (Sq. Ft):

165,092


Finances & Disclosures

Finances

Price:

$1,599,000

Price per Sq. Ft:

$312 per Sq. Ft.

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Copyright 2026 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 28, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.